Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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5:14 minutes

Problem 43e,f

Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(e)
(f)

Verified step by step guidance

Step 1: Analyze the alcohol structures provided. The first structure contains a cyclohexane ring with two hydroxyl groups (-OH), one on the ring and one on a side chain. The second structure contains a cyclohexane ring with a hydroxyl group (-OH) and an ester functional group (-COOCH3).

Step 2: For the first alcohol, identify the precursor carbonyl compound. The hydroxyl group on the side chain suggests that the precursor could be an aldehyde (e.g., CHO group attached to the cyclohexane ring). Reduction of the aldehyde would yield the primary alcohol (-CH2OH).

Step 3: For the second alcohol, identify the precursor carbonyl compound. The ester functional group (-COOCH3) suggests that the precursor could be a ketone (e.g., a carbonyl group adjacent to the ester group). Reduction of the ketone would yield the secondary alcohol.

Step 4: Suggest appropriate reducing agents for the transformations. Common reducing agents for aldehydes and ketones include sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4). NaBH4 is milder and typically used for aldehydes and ketones, while LiAlH4 is stronger and can reduce esters as well.

Step 5: Summarize the reaction pathways. For the first alcohol, the aldehyde precursor is reduced to the primary alcohol using NaBH4 or LiAlH4. For the second alcohol, the ketone precursor is reduced to the secondary alcohol using NaBH4 or LiAlH4. Ensure proper reaction conditions (e.g., solvent choice) for each reducing agent.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They include aldehydes and ketones, which are key intermediates in organic synthesis. Understanding the structure and reactivity of these compounds is essential for predicting the products of reduction reactions, where carbonyls are converted into alcohols.

Reducing Agents

Reducing agents are substances that donate electrons in a chemical reaction, thereby reducing another species. Common reducing agents for carbonyl compounds include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). The choice of reducing agent can influence the selectivity and efficiency of the reduction process, making it crucial to understand their properties and reactivity.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule. In organic chemistry, this often refers to the conversion of carbonyl groups to alcohols. Familiarity with the mechanisms of these reactions, including the role of the reducing agent and the conditions required, is vital for successfully synthesizing alcohols from carbonyl compounds.

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Related Practice

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(j)

Textbook Question

Predict the products you would expect from the reaction of LiAlH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(d)

Textbook Question

Predict the products of the following reactions:

(a)

(b)

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(b)

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(d)

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(f)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(k)

(l)

Textbook Question

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(f) 1-methylcyclohexanol → 2-methylcyclohexanone (several steps)

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Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.(e) (f)

Key Concepts

Carbonyl Compounds

Reducing Agents

Reduction Reactions

Watch next

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(e)
(f)